Work

Enzyme mediated-transesterification of verbascoside and evaluation of antifungal activity of synthesised compounds

Year: 2014

Type: article

Abstract: Enzymatic acylation of verbascoside, a polyhydroxylated natural product, has been reported in this study using five different commercial lipases and taking p-nitrophenyl alkanoates as acyl donors. Out of these enzymes, the immobilised Candida antarctica lipase B was found as the enzyme of choice. Mono- and di-acylated products were formed, with mono as major product indicating high regioselective nature of such transformations. A series of acyl esters of verbascoside have been synthesised by this enzymatic transesterification methodology. The lipophilicity of the synthesised analogues was also checked. The analogues were further subjected to synergistic antifungal activity with amphotericin B (AmB) against Candida albicans. Fourfold reduction in minimum inhibitory concentration of AmB was observed with few synthesised analogues such as verbascoside 4″-octanoate (3b), verbascoside 4″-palmitate (3d) and verbascoside 4″,4'-dipalmitate (4d) at a concentration of 0.5 μg/mL.

Source: Natural Product Research

DOI: 10.1080/14786419.2014.984181

Authors: Jabeena Khazir, Intizar Ali, Inshad Ali Khan, Halmuthur Mahabalarao Sampath Kumar

Institutions: Indian Institute of Integrative Medicine, University of Pretoria, Indian Institute of Chemical Technology

Language: English

Topic: Enzyme Catalysis and Immobilization

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

SDG: Good health and well-being

Open Access status: green

Funder: University of Pretoria